Retracted: Bis(4,4′-bipyridine-κN)tetra­kis(nitrato-κ²O,O′)tin(IV)

The Sn^IV atom in the title complex, [Sn(NO₃)₄(C₁₀H₈N₂)₂], is ten-coordinated by two N atoms of 4,4′-bipyridine ligands and eight O atoms of four NO₃⁻ ligands. The Sn atom lies on a crystallographic twofold rotation axis. The Sn—O bond lengths are in the range 2.378 (5)–2.538 (5) Å. The Sn—N bond length is 2.601 (5) Å. C—H...O hydrogen bonds link mononuclear complex mol­ecules into a supra­molecular network structure.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.034
• wR factor = 0.120
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Sn1    -   O1      ..      10.61 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Sn1    -   O4      ..      10.50 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Sn1    -   O6      ..      11.69 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O4
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        Sn1
PLAT430_ALERT_2_B Short Inter D...A Contact  N4     ..  N4      ..       2.60 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Sn1    -   O3      ..       9.38 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Sn1    -   N3      ..       8.09 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         11
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C5      ..       2.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  O1      ..       2.74 Ang.

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Sn1         (2)       2.67

   0 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

S1. Comment

In recent years, the researches on tin complexes draw increasing attention owning to their potential applications as photovoltaic materials, holographic recording system and biological activities (Jiang & Ozin, 1998; Valiukonis et al., 1986; Hencher et al., 1982; Bandoli et al., 1992, 1993), solar control devices (Nair & Nair, 1991) and semiconductor materials. Mononuclear or binuclear tin materials are important candidates as molecular precursors to prepare tin film materials by chemical vapour deposition (CVD)(Barone et al., 2002). We report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The ten-coordinate environment of the Sn atom is completed by two N atoms of 4,4'-bipyridine ligands and eight O atoms of four NO₃^- ligands (Table 1). The Sn—O bond lengths are in the range 2.378 (5) to 2.538 (5) Å. The Sn—N bond length is 2.601 (5) Å. The C—H···O hydrogen bonds link the mononuclear complex into a supramolecular network structure (Fig. 2).

Related literature

For related literature, see: Allen et al. (1987); Bandoli et al. (1992); Bandoli et al. (1993); Barone et al. (2002); Hencher et al. (1982); Jiang & Ozin (1998); Nair & Nair (1991); Valiukonis et al. (1986).

S2. Experimental

Crystals of the title compound (I) were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Tin dioxide (30.1 mg, 0.2 mmol), 4,4'-bipyridine (93.6 mg, 0.6 mmol), nitric acid (0.2 mol/l, 4 ml) and distilled water (2 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure for 7 d at 413 K and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature. Powder X-ray diffraction was conducted on the sample.

S3. Refinement

H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of the title molecule (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code (A): 2 - x, y, 1 - z].
	Fig. 2. Packing diagram for (I) showing hydrogen bonds as dashed lines.

Bis(4,4'-bipyridine-κN)tetrakis(nitrato-κ²O,O')tin(IV)

Crystal data

[Sn(NO3)4(C10H8N2)2]	F(000) = 1352
Mr = 679.10	Dx = 1.879 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8336 reflections
a = 20.112 (6) Å	θ = 2.4–29.3°
b = 7.813 (4) Å	µ = 1.15 mm^−1
c = 17.302 (9) Å	T = 273 K
β = 117.991 (7)°	Plate, colourless
V = 2400.9 (18) Å^3	0.40 × 0.33 × 0.21 mm
Z = 4

Data collection

Bruker APEX II area-detector diffractometer	2286 independent reflections
Radiation source: fine-focus sealed tube	2249 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 26.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
Tmin = 0.656, Tmax = 0.797	k = −9→9
7607 measured reflections	l = −21→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0667P)^2 + 18.0815P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2286 reflections	Δρmax = 0.91 e Å^−3
187 parameters	Δρmin = −0.48 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0039 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	1.0000	0.33854 (5)	0.7500	0.0270 (2)
O1	1.0922 (3)	0.4420 (6)	0.8899 (3)	0.0648 (12)
O2	1.0826 (4)	0.4128 (9)	1.0030 (3)	0.0938 (19)
O3	0.9970 (3)	0.3044 (6)	0.8849 (3)	0.0653 (12)
O4	0.9294 (3)	0.0723 (7)	0.6688 (4)	0.0745 (14)
O5	0.8183 (3)	−0.0051 (7)	0.6530 (4)	0.0817 (15)
O6	0.8783 (3)	0.2147 (6)	0.7288 (3)	0.0650 (12)
N1	1.0580 (3)	0.3864 (7)	0.9290 (4)	0.0600 (13)
N2	0.8730 (3)	0.0901 (7)	0.6819 (3)	0.0558 (12)
N3	0.9364 (3)	0.6015 (7)	0.7804 (3)	0.0552 (12)
C1	0.9745 (4)	0.7368 (8)	0.8256 (4)	0.0563 (15)
H1	1.0232	0.7527	0.8338	0.068*
C2	0.9464 (4)	0.8529 (8)	0.8606 (5)	0.0543 (15)
H2	0.9751	0.9465	0.8915	0.065*
C3	0.8638 (4)	0.5856 (9)	0.7678 (4)	0.0612 (16)
H3	0.8352	0.4939	0.7344	0.073*
C4	0.8315 (4)	0.6930 (8)	0.8003 (4)	0.0571 (15)
H4	0.7823	0.6765	0.7903	0.068*
C5	0.8742 (4)	0.8304 (7)	0.8496 (4)	0.0501 (14)
C6	0.8428 (3)	0.9443 (8)	0.8911 (4)	0.0498 (13)
C7	0.7946 (4)	0.8782 (9)	0.9187 (4)	0.0549 (14)
H7	0.7825	0.7624	0.9124	0.066*
C8	0.7653 (4)	0.9862 (9)	0.9554 (4)	0.0604 (15)
H8	0.7324	0.9431	0.9745	0.073*
N4	0.7817 (4)	1.1533 (7)	0.9655 (4)	0.0616 (15)
C9	0.8274 (5)	1.2168 (10)	0.9397 (6)	0.075 (2)
H9	0.8378	1.3334	0.9464	0.090*
C10	0.8605 (5)	1.1178 (9)	0.9031 (5)	0.0685 (19)
H10	0.8942	1.1648	0.8863	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0322 (3)	0.0257 (3)	0.0323 (3)	0.000	0.0227 (2)	0.000
O1	0.063 (3)	0.072 (3)	0.067 (3)	−0.012 (2)	0.037 (2)	0.000 (2)
O2	0.128 (5)	0.098 (4)	0.043 (3)	−0.012 (4)	0.029 (3)	−0.005 (3)
O3	0.072 (3)	0.073 (3)	0.063 (3)	−0.018 (2)	0.041 (2)	−0.006 (2)
O4	0.084 (4)	0.067 (3)	0.092 (4)	−0.002 (3)	0.058 (3)	−0.015 (3)
O5	0.079 (3)	0.078 (3)	0.082 (3)	−0.034 (3)	0.033 (3)	−0.017 (3)
O6	0.077 (3)	0.059 (3)	0.075 (3)	−0.011 (2)	0.049 (3)	−0.018 (2)
N1	0.070 (4)	0.058 (3)	0.054 (3)	−0.001 (3)	0.031 (3)	0.002 (2)
N2	0.063 (3)	0.052 (3)	0.057 (3)	−0.006 (2)	0.031 (3)	−0.005 (2)
N3	0.065 (3)	0.056 (3)	0.057 (3)	0.002 (2)	0.039 (3)	−0.003 (2)
C1	0.063 (4)	0.051 (3)	0.070 (4)	−0.005 (3)	0.044 (3)	−0.006 (3)
C2	0.061 (4)	0.051 (3)	0.064 (4)	−0.006 (3)	0.041 (3)	−0.008 (3)
C3	0.062 (4)	0.062 (4)	0.064 (4)	−0.002 (3)	0.033 (3)	−0.015 (3)
C4	0.054 (4)	0.063 (4)	0.058 (3)	0.001 (3)	0.030 (3)	−0.011 (3)
C5	0.059 (4)	0.051 (3)	0.050 (3)	0.004 (2)	0.033 (3)	0.001 (2)
C6	0.054 (3)	0.052 (3)	0.051 (3)	0.002 (3)	0.031 (3)	−0.002 (2)
C7	0.061 (4)	0.055 (3)	0.060 (3)	−0.003 (3)	0.038 (3)	−0.007 (3)
C8	0.063 (4)	0.068 (4)	0.065 (4)	−0.004 (3)	0.042 (3)	−0.007 (3)
N4	0.070 (4)	0.064 (4)	0.067 (3)	0.005 (3)	0.046 (3)	−0.009 (2)
C9	0.103 (6)	0.055 (4)	0.098 (6)	−0.007 (4)	0.073 (5)	−0.014 (4)
C10	0.094 (6)	0.052 (3)	0.090 (5)	−0.007 (3)	0.069 (5)	−0.012 (3)

Geometric parameters (Å, º)

Sn1—O1	2.396 (5)	C1—H1	0.9300
Sn1—O3	2.378 (5)	C2—C5	1.384 (9)
Sn1—O4	2.538 (5)	C2—H2	0.9300
Sn1—O6	2.495 (5)	C3—C4	1.335 (9)
Sn1—N3	2.601 (5)	C3—H3	0.9300
Sn1—O3^i	2.378 (5)	C4—C5	1.389 (9)
Sn1—O1^i	2.396 (5)	C4—H4	0.9300
Sn1—O6^i	2.495 (5)	C5—C6	1.460 (8)
Sn1—O4^i	2.538 (5)	C6—C7	1.367 (9)
O1—N1	1.247 (7)	C6—C10	1.392 (9)
O2—N1	1.154 (7)	C7—C8	1.347 (9)
O3—N1	1.272 (8)	C7—H7	0.9300
O4—N2	1.265 (7)	C8—N4	1.338 (9)
O5—N2	1.223 (7)	C8—H8	0.9300
O6—N2	1.240 (7)	N4—C9	1.294 (10)
N3—C1	1.324 (9)	C9—C10	1.355 (10)
N3—C3	1.378 (9)	C9—H9	0.9300
C1—C2	1.353 (8)	C10—H10	0.9300
O1—Sn1—O3	53.85 (16)	O2—N1—O1	118.7 (7)
O1—Sn1—O4	143.36 (18)	O2—N1—O3	123.1 (6)
O1—Sn1—O6	121.36 (15)	O1—N1—O3	118.2 (5)
O3—Sn1—O4	100.75 (17)	O5—N2—O6	122.0 (6)
O3—Sn1—O6	68.01 (16)	O5—N2—O4	124.7 (6)
O4—Sn1—O6	49.13 (15)	O6—N2—O4	113.3 (5)
O1—Sn1—N3	75.55 (18)	C1—N3—C3	116.2 (5)
O3—Sn1—N3	69.45 (17)	C1—N3—Sn1	123.2 (4)
O4—Sn1—N3	123.99 (18)	C3—N3—Sn1	118.9 (4)
O6—Sn1—N3	78.13 (17)	N3—C1—C2	123.5 (6)
O3—Sn1—O3^i	167.1 (2)	N3—C1—H1	118.2
O3—Sn1—O1^i	131.72 (17)	C2—C1—H1	118.2
O3^i—Sn1—O1^i	53.85 (16)	C1—C2—C5	119.0 (6)
O3^i—Sn1—O1	131.72 (18)	C1—C2—H2	120.5
O1^i—Sn1—O1	140.6 (2)	C5—C2—H2	120.5
O3^i—Sn1—O6	106.71 (17)	C4—C3—N3	124.4 (6)
O1^i—Sn1—O6	75.01 (17)	C4—C3—H3	117.8
O3—Sn1—O6^i	106.70 (17)	N3—C3—H3	117.8
O3^i—Sn1—O6^i	68.01 (16)	C3—C4—C5	117.5 (7)
O1^i—Sn1—O6^i	121.36 (15)	C3—C4—H4	121.2
O1—Sn1—O6^i	75.01 (17)	C5—C4—H4	121.2
O6—Sn1—O6^i	134.3 (2)	C2—C5—C4	119.2 (6)
O3^i—Sn1—O4	68.27 (18)	C2—C5—C6	121.6 (6)
O1^i—Sn1—O4	75.55 (18)	C4—C5—C6	119.2 (6)
O6^i—Sn1—O4	91.07 (17)	C7—C6—C10	119.3 (6)
O3—Sn1—O4^i	68.28 (18)	C7—C6—C5	118.9 (6)
O3^i—Sn1—O4^i	100.75 (17)	C10—C6—C5	121.8 (6)
O1^i—Sn1—O4^i	143.36 (18)	C8—C7—C6	117.8 (6)
O1—Sn1—O4^i	75.55 (18)	C8—C7—H7	121.1
O6—Sn1—O4^i	91.07 (17)	C6—C7—H7	121.1
O6^i—Sn1—O4^i	49.12 (15)	N4—C8—C7	122.5 (6)
O4—Sn1—O4^i	69.9 (3)	N4—C8—H8	118.8
O3^i—Sn1—N3	121.88 (16)	C7—C8—H8	118.8
O1^i—Sn1—N3	73.54 (16)	C9—N4—C8	120.0 (6)
O6^i—Sn1—N3	144.95 (18)	N4—C9—C10	121.7 (7)
O4^i—Sn1—N3	137.37 (17)	N4—C9—H9	119.1
N1—O1—Sn1	93.9 (4)	C10—C9—H9	119.1
N1—O3—Sn1	94.0 (3)	C9—C10—C6	118.6 (7)
N2—O4—Sn1	97.3 (4)	C9—C10—H10	120.7
N2—O6—Sn1	100.2 (4)	C6—C10—H10	120.7

Symmetry code: (i) −x+2, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O6	0.93	2.37	3.021 (8)	127
C1—H1···O1	0.93	2.74	3.111 (9)	105